639008-17-6Relevant articles and documents
Synthesis of 5-substituted indole derivatives. Part 4: Naratriptan from α-anilinoacetaldehyde dimethylacetal by TiCl4-mediated cyclisation
Pete, Bela,Simig, Gyula,Poszavacz, Laszlo,Toeke, Laszlo
, p. 2441 - 2455 (2007/10/03)
N-Methyl-3-(1-methyl-4-piperidinyl)-1H-indole-5-ethanesulfonamide (Naratriptan, 2) was prepared from N-methyl-N-phenylmethyl-2-(4-aminophenyl)-ethanesulfonamide (3b) through reductive alkylation with dimethoxyacetaldehyde followed by N-acylation and TiCl4-mediated indolisation, according to Sundberg procedure. The isopropyl group proved to be a useful protecting group for sulfonate esters in a number of transformations but was cleaved in the presence of TiCl4.